Here we are early into the 2012-2013 NHL season. Well, technically it’s just the 2013 NHL season; no games were played due to the lockout that just ended. And despite hockey’s return, I find myself strangely apathetic. Perhaps that’s partly because I’m a Leafs fan, and they just fired GM Brian Burke rather unceremoniously. I was a big proponent of Burke when he was hired and, while I think he failed to get either a #1 centre or a true starting goaltender (the jury’s still out on James Reimer), he did jettison a TON of flotsam and jetsam while adding some nice building blocks during his 3.5 seasons here. I only hope Dave Nonis doesn’t trade for Roberto Luongo; his contract would be an absolute dead weight for this franchise, similar to Rick DiPietro’s contract on Long Island. One thing that all of this did though was get me thinking where a Luongo deal would rank among the worst Leafs trades of the modern era.

Being a Leafs fan can be a wonderful thing, especially if you live in Southern Ontario. It gives you a common bond with a wide variety of people, and virtually everyone has a favourite moment. But there’s also the heartache, and the feeling that, as a fan, your relationship with the team is very one-sided. The eccentricity of former owner Harold Ballard (picture George Steinbrenner without ANY sort of filter, and zero willingness to spend) destroyed the team for an entire decade during the 1980s, and led to massive ownership squabbles in the 1990s. The team is now owned by a pair of telecommunications giants (Rogers and Bell). The new owners have shown an early willingness to meddle (as evidenced by Burke’s dismissal). However, they would be hard-pressed to be worse than the previous owner, which was a faceless corporation that was largely perceived as caring more about profits than winning. Additionally, Leafs’ tickets are largely corporately owned, which leads to the lower bowl being empty for the first five minutes of the 2nd and 3rd periods, while the ticket-holders are still enjoying beverages and food (including sushi) in the platinum lounge. And the few seats held by “real” fans are among the most expensive in professional sports. All of this combines to leave the Leafs as the most valuable franchise in the NHL (according to Forbes), but one of the worst fan experiences in professional sports (as per an ESPN survey).

But there is always hope. For me personally, I was optimistic about Brian Burke. He made some shrewd moves in Anaheim, took advantage of opportunities, and wasn’t afraid to take risks. And he was given free reign without owner interference for most of his tenure. It remains to be seen how much autonomy Dave Nonis will get in the post-Burke era. The fact remains that, other than Cliff Fletcher (who made the fantastic Fuhr, Gilmour and Andreychuk deals nearly 20 years ago), the Leafs haven’t been blessed with a wealth of skill or experience at the general manager’s position. Meanwhile, the Montreal Canadiens dominated the 1970s thanks in large part to the brilliance of GM Sam Pollack.

The Leafs can be a painful team to root for, and their failure to win a Stanley Cup since 1967 is a key cause of that pain. But the worst part is the Leafs themselves are one of the biggest reasons for this drought, thanks to their mismanagement of talent and squandering of assets. Take for example the picture above: it shows the four most popular Leafs captains of the past 30 years (although Mats Sundin could arguably be seen as more popular than Rick Vaive), and yet none of them were allowed to retire as Leafs captain (or even as a Leaf). After reviewing Toronto’s trades in the modern era (post-1967), a clear pattern emerges wherein the Leafs trade away young talent for aging, fading “big name” players who fail to deliver the goods. And the older talent then leaves at a devalued state, often for little-to-nothing in return. To say nothing of instances such as their decision not to sign a 14-year-old wunderkind named Bobby Orr, and their refusal to extend an offer to a free agent named Wayne Gretzky in 1997.

With that in mind, I have compiled a list of the 25 worst trades in Maple Leafs history. I’ve also identified a few that have been maligned by others in the past, for which I feel I can defend from their exclusion as a bad trade. Nearly five years ago, I created a Top 15 list for another website. In hindsight, I made a few oversights and allowed bias in the rankings. A few others have been re-evaluated with a greater history of playing time for the participants. So the list has been expanded and also re-ordered, with an eye towards eliminatomg some rather blatant bias I exhibited when prioritizing Toronto’s trade history the first time around.

One difference with this versus other lists is I don’t put much stock in whomever the Leafs’ trading partner chose with the draft pick. For example, the Leafs did a swap of first round picks in 1992, that saw the Leafs pick Brandon Convery, and the Islanders picked Darius Kasparaitus. I don’t count this as a terrible trade, because there is no guarantee the Leafs would have chosen Kaspar. All that matters is their own pick, because that is the only aspect of the deal they can control. So a deal can be a bust because the Leafs squandered their draft choice, but a deal won’t necessarily be a bust because the other team hit a home run with their pick.

This is the first in a series of six articles. In addition to this now-completed introduction, I will also defend a trio of deals that, while they have been touted in the past as poor trades, I feel they were worthwhile (or at least not bad enough to be considered a lopsided trade against Toronto). And with that… the trades that Do Not Qualify for the list of the Worst Toronto Maple Leafs Trades.

Does Not Qualify: Toronto trades a 1st Round Pick in 2010 (Tyler Seguin), a 2nd Round Pick in 2010 (Jared Knight), and a 1st Round Pick in 2011 (Dougie Hamilton) to the Boston Bruins for Phil Kessel (September 19th, 2010)I’m sure a number of you immediately greeted my defense of this trade with “Are you (bleeping) KIDDING ME?”. Many Leafs fans (especially those who call in to Toronto radio sports programming) consider this trade to be the worst deal made in the history of the NHL. I will preface my defense of this trade by saying that yes, we overpaid for Kessel. However, the gap wouldn’t have been quite so substantial if the Leafs hadn’t collapsed so spectacularly in 2009-10 season. Absolutely, losing a Top 5 pick stings, especially when it became a #2 overall choice in a draft where the top two players (Taylor Hall and Tyler Seguin) were ranked 1 and 1A by most pundits. I also admit that the situation becomes a little cloudier when you ask the question, “Would Brian Burke have made the trade knowing it was the #2 overall pick?”

But consider Phil Kessel right now. In three seasons, Kessel has scored 30, 32 and 37 goals. He scored 36 in his final year in Boston: he is a bona-fide NHL sniper. In the past 15 seasons (96-97 to 11-12), do you know how many Maple Leafs have scored 30 goals in a Toronto uniform? Mats Sundin did it ten times, demonstrating just how good he was over an extended period of time. But after him, just four, and NONE of them did it more than once: Nikolai Kulemin (2010-11), Alexander Mogilny (2002-03), one-hit-wonder Sergei Berezin (1998-99) and fan-favourite Wendel Clark (1996-97). That’s right; five three players in 15 seasons. And Kessel just turned 25 years old, which means he hasn’t even hit his prime yet. This isn’t the Leafs dealing for a veteran scorer on his way down; this is the Leafs acquiring a young player with a bright future, one who is locked in to a long-term contract. Also consider that Kessel has more goals than anyone else chosen in the 2006 entry draft. And that includes Jordan Staal, Jonathan Toews and Nicklas Backstrom.

Having addressed Kessel’s value and placement in recent Leafs’ history, there is another factor to consider: the fact that the Leafs are their own worst enemy at the draft table. Let’s examine their first-round selections from 1990-2006:

Jiri Tlusty (2006, 13th overall)

Tuukka Rask (2005, 21st overall)

Alexander Steen (2002, 24th overall)

Carlo Coliacovo (2001, 17th overall)

Brad Boyes (2000, 24th overall)

Luca Cereda (1999, 24th overall)

Nikolai Antropov (1998, 10th overall)

Jeff Ware (1995, 15th overall)

Eric Fichaud (1994, 16th overall)

Kenny Jonsson (1993, 12th overall)

Brandon Convery (1992, 8th overall)

Drake Berehowsky (1990, 10th overall)

Now from that list, there are three names that pop out: Rask, Boyes and Jonsson. Rask has just been handed the reins in Boston, and is on the verge of becoming a star. Meanwhile, Boyes once scored 40 goals, and Jonsson played nearly 700 games. BUT… they all emerged as quality NHLers after being traded from Toronto. Of the rest, only Antropov and possibly Coliacovo were above-average NHL players, and they certainly aren’t stars. My point is, over a 16-year period, the Leafs drafted quite poorly. And don’t forget that Kessel was a Top 5 choice himself in 2006. Was he worth the price Burke paid to get him? Seguin makes it extremely difficult to say yes, and Hamilton’s potential could push this deal firmly into the “no” side of things. But I wouldn’t say the deal was completely one-sided, and I certainly wouldn’t call it a failure for the Leafs. Not yet, anyways: this trade has a long ways to go before we can say that. Seguin looks like he could have all-world talent, but he hasn’t had the chance yet to demonstrate that as being the case over the long-term. He could be an all-star, or he could be the next Pat Falloon.

Let’s all settle down, and see what Kessel is capable of. Especially if the Leafs can surround him with a better supporting cast, and ideally a true #1 centre. The one knock against Kessel that I will acknowledge is where Sundin was able to carry and lead a team, Kessel seems better suited to being the next guy in line. That is to say, he might be better suited as a complement to a franchise player, rather than being the franchise player himself. For better or for worse, Kessel will always define Burke’s legacy as a Leafs GM. But with Burke gone, maybe Kessel will get a fair chance to show how good he could be, even if Toronto overpaid to get him. (OCT. 2013 UPDATE: Given that the Leafs have signed Kessel to an 8-year extension, and Tyler Seguin has been deemed a poor fit with Boston and sent to the Dallas Stars, this trade could ARGUABLY be deemed a Leafs’ win, or at worst an even trade)

Does Not Qualify: Toronto trades Rick Vaive, Steve Thomas and Bob McGill to the Chicago Blackhawks for Ed Olczyk and Al Secord (September 3rd, 1987)
This trade often gets a bad rap among old school Leafs fans. I’m not 100% sure why, but it is likely due to Vaive’s individual success as Leafs’ captain (and the fact that he is one of only three Leafs to score 50 goals in a single season). But when you look at the numbers, the trade actually wasn’t that bad at all. Vaive played 106 games in Chicago, scoring a respectable 55 goals. He was then dealt to Buffalo, where he began to fade; he was gone from the NHL less than three years later. Thomas was strong for the Blackhawks, but not a star; he recorded 198 points in 231 games before being shipped off to the New York Islanders. He didn’t really hit his stride as an upper-tier winger until he began playing in New York. Bob McGill was serviceable, but didn’t do much of note in four seasons with Chicago (other than 641 PIM). Interestingly enough, Vaive was dealt to Buffalo for Adam Creighton, who went to the Islanders in the same deal as Thomas.

On the Toronto side of the deal, Al Secord wasn’t a great fit: the Leafs dealt him to Philadelphia just a year and a half later. Ed Olczyk, on the other hand, was spectacular. He averaged 37 goals and 84 points in his 3 full seasons with Toronto. Early into his fourth season in Toronto, he was traded to the Winnipeg Jets in a deal that netted the Leafs Dave Ellett. Ellett ended up being a key part of the beloved ’93 and ’94 Leafs teams. Given Olczyk’s performance and Vaive’s distinct lack of staying power post-Leafs, I’d actually call this trade a win rather than a loss. And in an ironic twist, everyone except Vaive ended up having a second stint with the team that traded them (Olczyk and Secord each played again in Chicago, while Thomas and McGill were both Leafs for second tours in the 1990s).

Did Not Qualify: Toronto trades Wilf Paiement to the Quebec Nordiques for Miroslav Frycer and a 7th Round Pick in 1982 (Jeff Triano) (March 9th, 1982)This was a deal that I fully expected was going to be one-sided. Paiement had the misfortune of replacing fan-favourite Lanny McDonald in a deal with the Colorado Rockies. He also wore #99 as a Leaf, which was either incredibly brave or exceptionally dumb. The jury is still out on that one. And Frycer’s legacy with the Leafs, as with most European players who played in Toronto during the 80s not named Salming, was not stellar. But to my surprise, the trade ended up being a positive one for Toronto.

Frycer wasn’t an all-star, and he didn’t have a ton of durability. But he had a pair of 25-goal, 55-point seasons, and his best season saw him score 32 goals and 75 points. In total, he put up a respectable 268 points in 329 games for some pretty terrible Toronto squads. Paiement was a solid player for the Nordiques, scoring 102 goals and 223 points in parts of five seasons. Jeff Triano, whom Toronto chose with the 7th round pick, never played in the NHL. So the deal was at best even, and at worst leaning slightly in Quebec’s favour (as Paiement’s numbers were a little better than Frycer’s). But certainly not a terrible deal by any stretch.

I hope that whet your appetite for more. Check out Part Two, where we look at the trades that ranked #21-25 on the list of Worst Toronto Maple Leafs trades of all time.